86060-86-8

Basic information

• Product Name: FMOC-ALA-OPFP
• Synonyms: N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-ALANINE PENTAFLUORPHENYL ESTER;N-ALPHA-FMOC-L-ALANINE PENTAFLUOROPHENYL ESTER;FMOC-ALANINE-OPFP;FMOC-ALA-OPFP;FMOC-L-ALANINE PENTAFLUOROPHENYL ESTER;FMOC-L-ALA-OPFP;NALPHA-9-Fluorenylmethoxycarbonyl-L-alanine pentafluorophenyl ester;N-(9-fluorenylmethoxycarbonyl)-L-alanine pentafluorophenyl
• CAS NO: 86060-86-8
• Molecular Formula: C₂₄H₁₆F₅NO₄
• Molecular Weight: 477.38
• Product Categories: Amino Acids;Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 86060-86-8.mol

Chemical Properties

• Melting Point: 181.0 to 185.0 °C
• Boiling Point: 574.072 °C at 760 mmHg
• Flash Point: 300.988 °C
• Appearance: white to yellow powder
• Density: 1.426 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: 2-8°C
• PKA: 10.32±0.46(Predicted)
• BRN: 3639513
• CAS DataBase Reference: FMOC-ALA-OPFP(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-ALA-OPFP(86060-86-8)
• EPA Substance Registry System: FMOC-ALA-OPFP(86060-86-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 86060-86-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C24H16F5NO4/c1-11(23(31)34-22-20(28)18(26)17(25)19(27)21(22)29)30-24(32)33-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16H,10H2,1H3,(H,30,32)/t11-/m0/s1

Upstream product

• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 103321-50-2 9H-fluoren-9-ylmethyl [(1S)-2-chloro-1-methyl-oxoethyl]carbamate 

Downstream Products

• 124676-24-0 1-(N-Fluorenylmethyloxycarbonyl-L-alanylamino)-1-((benzyloxycarbonyl)amino)acetic acid 
• 130738-27-1 Fmoc-Ala-Gly-Gly-Phe-Ala-Ser(OBzl)-Gly-Glu(OBzl)-OBzl 
• 130846-69-4 Fmoc-Ala-Gly-Gly-Asp(OBzl)-Ala-Ser(OBzl)-Gly-Glu(OBzl)-OBzl 
• 93710-17-9 methyl 2-(2-((((4aH-fluoren-9-yl)methoxy)carbonyl)amino)propanamido)-3-phenylpropanoate 

Relevant articles and documents

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Toluene-4-sulfonate (DMT/NMM/TsO?) Universal Coupling Reagent for Synthesis in Solution

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO?), a representative member of the inexpensive and environmentally-friendly N-triazinylammonium family of sulfonates, has been found to be a very effective coupling reagent for the synthesis of amides, esters and peptides in solution. This study confirms the usefulness of DMT/NMM/TsO? for peptide synthesis in solution, starting from Z-, Fmoc-, and Boc-protected substrates as well as unnatural building blocks. Peptide synthesis with DMT/NMM/TsO? produced high yields, with high crude product purity and low risk of racemization. In all cases, stoichiometric amounts of reagents were used and the standard synthetic procedure, without the need for time-consuming optimization stages or expensive chromatographic purification. DMT/NMM/TsO? was also found to be very useful for the synthesis of oligopeptides using a fragment coupling strategy.

A new facile one-pot preparation of pentafluorophenyl (Pfp) and 3,4-dihydro-4-oxo-1,2,3-benzotriazine-3-yl (Dhbt) esters of Fmoc amino acids

A new one-pot procedure for the preparation of pentafluorophenyl and 3,4-dihydro-4-oxo-1,2,3-benzotriazine-3-yl esters of Nα-9-fluorenylmethyloxycarbonyl amino acids bearing no side chain protecting groups is described. The method gives the desired activated esters in high yield and purity without use of the highly allergenic DCC.

9-Fluorenylmethyl Pentafluorophenyl Carbonate as a Useful Reagent for the Preparation of N-9-Fluorenylmethyloxycarbonylamino Acids and their Pentafluorophenyl Esters

9-Fluorenylmethyl pentafluorophenyl carbonate is a useful reagent for the efficient, side reaction-free introduction of N-9-fluorenylmethyloxycarbonyl protecting group into amino acids and for the subsequent preparation of their pentafluorophenyl esters.Some new compounds of both types are described.